NAV

Brodimoprim-4,6-Dicarboxylate

Identification

Generic Name
Brodimoprim-4,6-Dicarboxylate
DrugBank Accession Number
DB02809
Background

Brodimoprim-4,6-dicarboxylate is a solid. This compound belongs to the anisoles. These are organic compounds contaiing a methoxybenzene or a derivative thereof. This medication is known to target the protein dihydrofolate reductase.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 496.332
Monoisotopic: 495.087922167
Chemical Formula
C20H24BrN4O6
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UDihydrofolate reductaseNot AvailableLactobacillus casei
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenol ethers
Sub Class
Anisoles
Direct Parent
Anisoles
Alternative Parents
Phenoxy compounds / Methoxybenzenes / Medium-chain fatty acids / Alkyl aryl ethers / Aminopyrimidines and derivatives / Branched fatty acids / Bromobenzenes / Halogenated fatty acids / Heterocyclic fatty acids / Aryl bromides
show 15 more
Substituents
Alkyl aryl ether / Amine / Amino acid / Amino acid or derivatives / Aminopyrimidine / Anisole / Aromatic heteromonocyclic compound / Aryl bromide / Aryl halide / Azacycle
show 33 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
organobromine compound, aminopyrimidine (CHEBI:47236)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
SZAVCZNFKJSWRN-LBPRGKRZSA-M
InChI
InChI=1S/C20H25BrN4O6/c1-30-14-8-11(7-13-10-24-20(23)25-18(13)22)9-15(17(14)21)31-6-2-3-12(19(28)29)4-5-16(26)27/h8-10,12H,2-7H2,1H3,(H,26,27)(H,28,29)(H4,22,23,24,25)/p-1/t12-/m0/s1
IUPAC Name
2,4-diamino-5-[(4-bromo-3-{[(4S)-4,6-dicarboxylatohexyl]oxy}-5-methoxyphenyl)methyl]pyrimidin-1-ium
SMILES
COC1=CC(CC2=C[NH+]=C(N)N=C2N)=CC(OCCC[C@@H](CCC([O-])=O)C([O-])=O)=C1Br

References

General References
Not Available
PubChem Compound
5287754
PubChem Substance
46507558
ChemSpider
4450057
PDBe Ligand
BDM
PDB Entries
1dis / 1diu

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00803 mg/mLALOGPS
logP0.94ALOGPS
logP1.03Chemaxon
logS-4.8ALOGPS
pKa (Strongest Acidic)3.02Chemaxon
pKa (Strongest Basic)8.16Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count9Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area177.79 Å2Chemaxon
Rotatable Bond Count12Chemaxon
Refractivity140.09 m3·mol-1Chemaxon
Polarizability45.62 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.6298
Blood Brain Barrier+0.7277
Caco-2 permeable-0.5596
P-glycoprotein substrateSubstrate0.5253
P-glycoprotein inhibitor INon-inhibitor0.9207
P-glycoprotein inhibitor IINon-inhibitor0.9114
Renal organic cation transporterNon-inhibitor0.7495
CYP450 2C9 substrateNon-substrate0.8765
CYP450 2D6 substrateNon-substrate0.842
CYP450 3A4 substrateNon-substrate0.5954
CYP450 1A2 substrateNon-inhibitor0.5894
CYP450 2C9 inhibitorNon-inhibitor0.7227
CYP450 2D6 inhibitorNon-inhibitor0.8249
CYP450 2C19 inhibitorNon-inhibitor0.5694
CYP450 3A4 inhibitorNon-inhibitor0.8676
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7291
Ames testNon AMES toxic0.6723
CarcinogenicityNon-carcinogens0.9568
BiodegradationNot ready biodegradable0.9143
Rat acute toxicity2.3534 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8204
hERG inhibition (predictor II)Non-inhibitor0.8022
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-190.9997
predicted
DeepCCS 1.0 (2019)
[M+H]+193.39526
predicted
DeepCCS 1.0 (2019)
[M+Na]+200.205
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Dihydrofolate reductase
Kind
Protein
Organism
Lactobacillus casei
Pharmacological action
Unknown
General Function
Nadp binding
Specific Function
Key enzyme in folate metabolism. Catalyzes an essential reaction for de novo glycine and purine synthesis, and for DNA precursor synthesis.
Gene Name
folA
Uniprot ID
P00381
Uniprot Name
Dihydrofolate reductase
Molecular Weight
18438.73 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52